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After being educated at University of Glasgow and time spent at the royal court of France, Montgomery served as a Captain of Foot of a Scottish Regiment under William I of Orange during the early parts of the Eighty Years' War. He returned to Scotland upon the death of his parents in 1587. He inherited his father's title as the Laird of Braidstane and married Elizabeth Shaw, who died in 1625.

Montgomery established a relationship with King James VI. He was able to gain some influence in the king's court due to his correspondence with his brother George Montgomery, who had been named Dean of Norwich in 1602. The information contained in the correspondence was important to James as it included details on English politics.

Montgomery became involved in the centuries-old feud between Clan Montgomery and Clan Cunningham. The feud dates to the 15th century when a Montgomery was named Bailie of Cunninghame by James II, a post the Cunninghams claimed was rightfully theirs. The 4th Earl of Eglinton was assassinated by the Cunninghams at about the time of Montgomery's return to Scotland.

Montgomery's involvement in the feud began when he took offence at something that a Cunningham said. Cunningham fled to London, then to Holland, where Montgomery caught up with him and confronted him in the Inner Court of the Palace at The Hague. Combating Cunningham with a sword, Montgomery delivered what he believing to be a killing thrust, but Cunningham's belt buckle deflected the blow. Montgomery believed he had killed Cunningham and made to leave the palace. He was arrested and imprisoned at Gevangenpoort in the Binnenhof. Montgomery broke out of jail with the help of a Scottish soldier.

Montgomery received a reprimand from King James but was soon back in favour. He accompanied the king to his coronation as King of England in spring 1603 after the death of Queen Elizabeth.

Montgomery's friendship with the king was useful to him next in establishing a Settlement in Ireland in 1606 (preceding the Plantation of Ulster in 1610). Looking for opportunity for advancement, Montgomery came into contact with the wife of Con O'Neill, a landowner in Ulster, who was imprisoned at Carrickfergus Castle for instigating rebellion against the Queen. Montgomery and Ellis O'Neill (the wife) made a deal that the O'Neills would give half of their land to him if he could free Con and secure for him a royal pardon. Montgomery sent a relative to Ireland to lead the jailbreak, which was successful.

At this point, James Hamilton interfered with the negotiations with the King, securing for himself a share of the land in question with the resultant shares being one-third each for Hamilton, Montgomery and O'Neill, who gained pardon. (Montgomery also secured for his brother George, title as Bishop of Derry and Raphoe.) Montgomery and Hamilton recruited Scots of many families and trades to populate their settlement. In May 1606 the first wave of settlers arrived. Montgomery settled at Newtownards and soon established a trade route between Donaghadee in Ireland and Portpatrick in Scotland.

In 1613, Montgomery, along with Hamilton, represented the settlement to the Irish House of Commons. At Donaghadee he built a large stone quay to accommodate vessels ferrying between Scotland and Ireland from 1616 onwards.[1] On 3 May 1622, Montgomery was made Viscount Montgomery.